The Surprising Power of Remote Work: Higher Trust Teams w/ Sarah Milstein #137

Sarah Milstein, VPE @ Daily, joins us to discuss the most surprising aspect of remote teams – the opportunity for higher trust teams. She covers counterintuitive perspectives & non-obvious practices that can benefit distributed orgs, including why hard conversations can be easier when done remotely and how remote teams are less political & more productive than co-located teams. Sarah also dives into Daily’s unique salary & promotion process and how eng leaders could implement this method into their teams. Lastly, we cover “swift trust” and Sarah’s recommendations for creating the optimal conditions for it to thrive.

ABOUT SARAH MILSTEIN

Sarah (@SarahM) joined Daily as VP of Engineering, bringing 25 years of deep experience developing products, setting strategy, and leading teams at startups. Most recently, Sarah was VP of Engineering at ConvertKit. Prior to that, she was Senior Director of Engineering at Mailchimp. Sarah has extensive experience in media as a producer and author, having programmed, co-hosted, and managed conferences and trade shows, including the Web 2.0 Expo. Sarah holds an M.B.A. from University of California, Berkeley.

"Swift Trust is an idea from workplace psychology about teams that come together quickly counterintuitively often build higher levels of trust and do it with very little structure, and it turns out that actually the coming together quickly and the less structure are themselves some of the conditions that can help. It turns out that those are the kind of conditions that are often true in software development. Those conditions of it's clear what you're working on, everyone has a role, there's time involved, like some sense of timing. A lot of times those conditions are available to you but maybe not being used.”

- Sarah Milstein   

Join us at ELC Annual 2023!

ELC Annual is our flagship conference for engineering leaders. You’ll learn from experts in engineering and leadership, gain mentorship and support from like-minded professionals, expand your perspectives, build relationships across the tech industry, and leave with practical prove strategies.

Join us this August 30-31 at the Fort Mason Center in San Francisco

For tickets, head to https://sfelc.com/annual2023SHOW NOTES:

• The most surprising aspect of working remotely: higher trust (3:24)
• Sarah’s Slack experiment & how it revealed team dynamics (6:15)
• Additional benefits & accommodations provided by remote work (8:26)
• Non-obvious communication practices that benefit remote orgs (11:18)
• Strategies for having hard conversations one-on-one in a remote setting (13:52)
• Recommendations for facilitating big group conversations remotely (16:34)
• Why distributed teams are less political & more productive than co-located teams (18:58)
• Internal practices to reduce politics (21:48)
• How Daily’s salary & promotion process works (23:40)
• Frameworks for aligning projects toward peoples’ strengths within a remote team (27:04)
• Process for implementing a new salary & promotion model (30:28)
• Defining “swift trust” & creating conditions for it to be present (34:20)
• Benefits of creating agreements on how you’re going to work as a team (37:04)
• Rapid fire questions (40:28)

LINKS AND RESOURCES

• The Staff Engineer's Path - For years, companies have rewarded their most effective engineers with management positions. But treating management as the default path for an engineer with leadership ability doesn't serve the industry well--or the engineer. Tanya O’Reilly’s staff engineer's path allows engineers to contribute at a high level as role models, driving big projects, determining technical strategy, and raising everyone's skills.
• Rethinking levels, promotions and salaries - Sarah’s blog post on Daily’s restructuring of levels, promotions, salaries, and how Daily approaches career compensation.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/